After several years working as a bodyguard for Danzig, Slayer, and occasionally for other bands such as Soundgarden,[2] James opened West Coast Choppers in his mother's garage in 1992. The company grew quickly and soon moved to a larger facility for select customers and companies. About 200 bikes have been built at West Coast Choppers. West Coast Choppers is also sponsoring race teams in Top Fuel Drags and Super Late Model NASCAR. Jesse James has also built and is racing an off-road Trophy Truck and a Figure-8 race car.

He was the owner of the Cisco Burger restaurant, which opened on April 28, 2006, just down the street from West Coast Choppers. The 1950s style hamburger stand—named after his beloved pit bull who is now deceased—featured Angus beef burgers, low-fat burritos, organic vegetables, and biodegradable wrappings. It has officially closed. James also had partial ownership in Austin Speed Shop in Austin, Texas which he left in 2013 to focus on the re-opening of West Coast Choppers in Austin. Other business ventures include the Chopperdogs fan club and the Jesse's Girl clothing line. Since 2006, James has nationally published Garage magazine.[3] In November 2013 Jesse James Firearms Unlimited unveiled its first two firearms, a 1911 pistol and AR-15 rifle.

In 2000, the Discovery Channel made the documentary Motorcycle Mania, which chronicled James's everyday life. Following the success of the documentary, the Discovery Channel approached James with an offer to host a new show called Monster Garage where James and a crew of mechanics modified vehicles under a short deadline. James later established Payupsucker Productions, under which he produced shows like History of the Chopper, Iraq Confidential with Jesse James and Green Scream, in which James plans to break the land speed record with an eco-friendly hydrogen car. Through James's show "History Of The Chopper" there are also glimpses of his involvement with the Hells Angels.

He also had an appearance on Discovery Channel's Sons of Guns. He appeared on the second season of Celebrity Apprentice. Each celebrity played to raise money for a favorite charity; James selected to play for the Long Beach Education Foundation.[4] Due to his poor performance in raising funds, James was eliminated by Donald Trump on the second-to-last show (ultimately placing 3rd) which aired May 3, 2009. Trump repeatedly cited James's stoic refusal to contact then-wife Bullock to raise funds for the show's challenges, though other celebrities had no problem tapping high-rolling contacts for cash.

James' Discovery Channel website states that his great-great-grandfather was the notorious outlaw's cousin.[9] However, Eric James, president of the James Preservation Trust, which tracks claims of being a relative of the outlaw, says it cannot find a record of him in the family tree, and has asked him to provide a family genealogy and DNA sample for the Trust to review; he has not provided the requested information.[10][11][12]

James has three children: a daughter and a son with his first wife, Karla James, to whom he was married from 1991 to 2002; and a daughter with his second wife, stripper/porn star/producer Janine Lindemulder, to whom he was married from 2002 to 2004.[13]

In October 2009, James's ex-wife Lindemulder, who had been in federal prison for six months for tax evasion, sought to regain custody of her then five-year-old daughter with James—Sunny—after James had been granted sole guardianship of her. James sought to retain full guardianship, citing fear of the environment in which his daughter would be placed if returned to Lindemulder.[15][16] In December, James won custody, and Lindemulder was given weekly visitation rights during the daytime.[17]

In March 2010, a media scandal arose when several women claimed to have had affairs with James during his marriage to Bullock. Bullock cancelled European promotional appearances for The Blind Side citing "unforeseen personal reasons".[18][19] On March 18, 2010, James responded to the rumors of infidelity by issuing a public apology to Bullock.[20] James declared that "There is only one person to blame for this whole situation, and that is me", and asked that his wife and children one day "find it in their hearts to forgive me" for their current "pain and embarrassment".[20] James’ publicist subsequently announced on March 30, 2010 that James had checked into a rehab facility "to deal with personal issues" and "save his marriage" to Bullock.[21] However, on April 28, 2010, it was reported that Bullock had filed for divorce[22] on April 23 in Austin.[23] Bullock also stated that she had proceeded with plans to adopt a baby boy born in New Orleans.[24] Bullock and James had begun an initial adoption process four years earlier. The child began living with them in January 2010, but they chose to keep the news private until after the Oscars in March 2010. However, given the couple's separation and then divorce, Bullock continued the adoption of the baby as a single parent.[24] The divorce was finalized on June 28, 2010, with "conflict of personalities" cited as the reason.[25]

In August 2010, tattoo artist Kat Von D confirmed reports that she and James were dating.[26][27] James and Von D became engaged in January 2011.[28] Von D announced that they had split in July 2011.[29][30] However, in August 2011, James and Von D announced that their engagement was back on.[31] In September 2011, Von D announced that she and James had broken up again.[32] Von D later accused James of cheating on her with multiple women during their relationship.[33]

In late 2012, James became engaged to professional drag racer Alexis DeJoria. They married on March 24, 2013 at the estate of the bride's father, entrepreneur John Paul DeJoria.[34]

In 2007, James was fined $271,250 by the California Air Resources Board (CARB) after state officials determined that he had sold motorcycles in violation of California's clean-air laws. According to police, James's customized bikes were emitting 11 times the legal limits of hydrocarbons. Investigators also found that the motorcycles did not have state-certified emissions equipment on their fuel tanks. The bikes were sold between 1997 and 2006.[35] James explained that he was unaware of rule changes that required small-volume manufacturers to comply with regulations. James said the CARB refused his offer to recall and modify the uncompliant choppers. Since 2005 West Coast Choppers has built emissions-compliant choppers.[36] James said the fines were excessive and intended to make an example of him due to his company's fame and his celebrity marriage to actress Sandra Bullock, but CARB spokesmen stated their enforcement efforts were aimed at the entire custom industry, and further that they were aware of no offer by West Coast Choppers to recall the motorcycles in question.[37]

In July 2008, James faced a $422,680 breach of contract lawsuit from Michael Jones, a customer who hired James to build him a custom car, who contended that after paying $270,000 over two years, the car was not completed, and that James informed him that it would cost between $600,000 and $700,000.[38] That September, James faced another lawsuit from his former lawyer for $327,533 in unpaid fees.[39]